Practice Exam 4(2)

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Texas A&M University *

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228

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Chemistry

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Feb 20, 2024

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Copyright K. Ponnamperuma Chem228 Practice Exam 4 Summer 2023 Page 1 of 7 Chem 228 Summer 2023 PRACTICE EXAM 4 1. Draw the correct structure for each of the following carboxylic acid derivatives. N-Ethyl cyclopentanecarboxamide (Z)-3-pentenoyl bromide 2. Arrange the following carboxylic acid derivatives in their correct order of reactivity. 1=Most reactive and 4=least reactive. 3. Arrange the hydrogens indicated in their correct order of acidity. 1=Most acidic and 4=least acidic. TURN OVER
Copyright K. Ponnamperuma Chem228 Practice Exam 4 Summer 2023 Page 2 of 7 4. Draw the two resonance forms for the enolate shown below. Do not draw curly arrows. 5. Shown below is the tetrahedral intermediate in a nucleophilic acyl substitution reaction. Draw the carbonyl reactant and the carbonyl product for the reaction. 6. Draw the two carbonyl compounds which could be used to make the enone shown below via the aldol reaction. 7. Which one of the ketones below can undergo racemization with aqueous base? TURN OVER
Copyright K. Ponnamperuma Chem228 Practice Exam 4 Summer 2023 Page 3 of 7 8. Draw the major organic product for each of the following reactions. TURN OVER
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Copyright K. Ponnamperuma Chem228 Practice Exam 4 Summer 2023 Page 4 of 7 9. Draw the two ethyl esters which could be used to make the mixed Claisen product shown below. 10. Draw the structure of the enamine and conjugated ketone which may be used to make the Robinson annulation product below via the Stork enamine reaction. 11. How would you synthesize the carboxylic acid shown below via the malonic ester synthesis? You must show the reactions/reagents used in their correct order. TURN OVER
Copyright K. Ponnamperuma Chem228 Practice Exam 4 Summer 2023 Page 5 of 7 12. For parts (a) and (b) draw a complete stepwise mechanism. You must show the structures of all intermediates and indicate electron flow with curly arrows. (a) (b) TURN OVER
Copyright K. Ponnamperuma Chem228 Practice Exam 4 Summer 2023 Page 6 of 7 13. Draw the structure of the major organic product for each of the following reactions. TURN OVER
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Copyright K. Ponnamperuma Chem228 Practice Exam 4 Summer 2023 Page 7 of 7 14. Draw the structure of the organobromide which can be used to make the methyl ketone shown below via the acetoacetic ester synthesis. ----------END OF EXAM----------